Second Date as a Whore
Copyright© 2026 by LolaPaul
Chapter 10: Back With An Older Client
Erotica Sex Story: Chapter 10: Back With An Older Client - I thought my old college friend Roger would be my first and last time as a whore, but Cupid made other plans. The Joker took advantage by messing with my guy’s biggest client. I had to get this done or jobs would be lost. This time it was the real thing, I had to whore for a stranger who was known to pay more for a girl going outside the rules. A lot more. He was a nice older man who wanted my ass, and as an extra surprise he brought some family! (All over 18.)
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Teenagers Heterosexual Fiction Sharing Slut Wife Wife Watching Group Sex Anal Sex Cream Pie Double Penetration Exhibitionism Oral Sex Sex Toys Prostitution
Mr. G returned to my bed promptly at 6. I was still resting on my belly with a pussy full of his Mick’s cum. Her dad did not seem surprised or upset to see Ariel with me. We both woke up so Mr. G and I chatted a little, he again said how attractive I was and asked if the boys had been considerate of me. I replied that I had enjoyed the company of each three times. After seeing that I was awake and making sure I was ready for intimate contact Mr. G carefully mounted me, putting his cock in my pussy to coat his cock with Mick’s seed (“for lube” he said) while he was using his fingers to lubricate and open my rosebud. Touching me there was a bit of a shock, but I knew it was coming so I tried to be cooperative and relaxed.
“I gather this was Mick, such a good idea,” he whispered.
I must have looked a little scared because Ariel was staring in my eyes with some fear for my bottom. I tried to look okay, but I didn’t do a good job. She was about to stop her dad but I calmed her with a touch on my hand.
As Mr. G was in my pussy, loading up with his son’s cum, he said, “If I am any judge it seems like the boys have had a good night. I am going to stretch you a little bit for our mutual benefit, then I will fuck your lovely ass. Do you understand?”
“Oh yes ... that is just what I was expecting.” I tried to sound a little hopeful.
I would not say he was solicitous of my approval, but this is what I had agreed to, and I could hardly say he was being brusque or causing undue pain. He took his time with the finger work to reduce my discomfort. By the time he moved his cock to my ass my tight little muscle was grudgingly stretched open and relaxed enough for his ‘torpedo-head’ to enter. I recalled how relaxed and co-operative I was with Gabe so I tried to invoke that muscle memory. The thought served me well. The entry of Mr. G’s much larger member did cause more than a pinch of pain at entry, but I was able to put it aside in my mind and I took it without a sound. No doubt the shape, especially the minimal ridge, made things easier for me.
Ariel saw the effect, but I kept her still, it really was minor.
When Mr. G entered me, he gently popped in and kept going, which I had never felt before from my husband. It seemed a little brutal, but really the total discomfort was less because his cock was so streamlined and free of surface protuberances like blood vessels. As his body pressed against my bottom and my back I really felt his desire for this act. He was good at it, all things considered.
I noticed that Ariel had an intensity as she watched. For the first time I wondered if she was seeing something she expected in her future. There was a classic story where a comely female ward turns 18. With no claim to any of the family wealth and after her sheltered teen years she has no training in the real world. It takes only a little disaccomaodation before she turns to the only man for which she has felt something like affection. She sees giving herself to him as her best solution. Except he was not really that nice, as the girl became more dependent he became more demanding of her.
I was sure that Ariel had cause to read such that story.
I will say that once Mr. G was inside my ass and was stroking away he was very generous with his praise about how good I felt and looked, he wished I could see what we looked like. I admitted honestly that I had never had this particular act done so well, he had prepared me better than ever for mutual pleasure. To get him more excited I casually mentioned that my phone was on the nightstand. “Maybe Ariel could take a picture that would not identify who was involved?” He was surprised at the novel idea. Ariel was suddenly very eager and willing to help.
I volunteered that, while the NDA said no pictures revealing identity, both he and I could trust Ariel. We could inspect them together afterwards. Ariel was plainly delighted at the prospect, that put him in a positive frame of mind. So he agreed and soon Ariel was snapping away with my cell-phone and then her own “best camera” cellphone.
Ariel took over two-dozen snaps before she was satisfied, including some with her own phone. Later, over breakfast her Father and I looked at those taken with my phone. He and I agreed on which were the best pictures. One showed his cock halfway into my obscenely stretched asshole, with a nice view of my round bottom and a very flattering angle on his body. I sent it to his phone on the spot. He was delighted. Later we settled on a longer shot, showing my body from my neck down to my thigh, it was especially flattering of my breasts, which was hanging down as I was lifting my chest up off the bed slightly. He especially liked it so I agreed to let him have that as well. Be both also kept some that Ariel shot with her camera.
Mr. G took his time enjoying sodimizing me. I was surprised that he was inside me, enjoying the tight fit while moving slowly, getting a lot out of it. I won’t say that I enjoyed it all, but the bad parts were over in a few seconds, and I must say I took some pleasure in the experience and in the way the three of us all shared it. He lasted for about ten minutes before he finished and filled my ass with his spunk.
For me there were 3 stages of the exercise. The entry and the first half minute or so I had to hide my trepidation and, for an instant, my pain, but then the discomfort diminished completely. Sexually I got nothing out of stage 2, which was by far the longest, except that I relaxed into his motion and he really enjoyed it. What I did enjoy was working with Ariel on the pictures as she directed us. Then in stage 3 I actually felt some pleasure in giving myself to him as relief. Like when my husband just wants a easy fuck, I sometimes take satisfaction in being there for him, because I know he needs it.
Mr. G was using my body to masturbate, to meet a natural desire. But for some reason I felt very relaxed and welcoming of his use. It was a commercial transaction where I felt like I was earning my money, but it was not really difficult in any sense. I heard myself start to moan, in a positive way. The impetus for my sounds was natural, there was something good in giving myself to him for his pleasure, although I admit that I played it up a bit. He enjoyed that I was enjoying him. We were both able to reach the point where it became more a mutual exercise than anything else. Also, from the way he used his hands he made it clear that he appreciated my body, even if I was a bit older than his usual young swimsuit models. He actually said that I changed his mind about older women (meaning those over 25).
His had a distinct and energetic finish when he surging and fired his release into my ass. His grunts and moan showed it was clearly a big deal for him. His groan of pure carnal pleasure at the moment he came was very loud and sincere. I felt the pulses, about a dozen, go through my gatekeeper muscle, and that brought me a somewhat satisfying feeling, like he was surrendering to me. He kissed me, many little kisses on my back, neck and cheek afterward. He said he was sorry if that crossed a line, but I told him that, all-in-all, it was a positive experience and I had no complaints.
“You have surprised me Miss Evie.”
“Well, it was my pleasure, Mr. G. In this world a man who knows what he wants and how to get it has some appeal. I can’t be sure if we will meet again, but if it happens I would look forward to it ... with all the trimmings.”
When he finished I must say he was invigorated. The three of us adjourned to the shower to clean up, he insisted on washing both of us. “You do such a good job of looking wonderful, please allow me to do what I enjoy.” Ariel and I supported each other while his hands washed us. First he did Ariel, although he left her private areas to her. When he turned to washing me he did everything, holding my body as he diligently cleaned the spunk his boys had left in my pussy. His fingers knew how to deliver the thrills to a woman, so we both enjoyed the embrace. When he finished with my pussy my ass was still open enough that his fingers slid in and easily cleaned the lube out as far as he could reach. We were staring into each other’s eyes when he his fingers entered me there, so we made a bit of a sincere connection. Last he actually got on his knees to flush my ass, which was unexpected. I knew his cum went deep enough that it would stay with me for some time, I would have to wear a pad when I dressed.
We had just finished stepping out of the bathroom when room service showed up at 7 with breakfast. Ariel and I wore robes to set up the table while Mr. G and his sons quickly dressed for an early start to the day. It was so easy working with her, we understood each other so well.
Over breakfast we had some talk about my newness to the business, given that my body seemed a decade older than the regulars, and Mr. G said “my mind was an least two decades ahead.” I made the point that in an ideal world there would be no need for this type of business to be cloaked in the shadows, it would probably be better if people could take classes in it. But even here, where the community accepted and needed our services, the profession was spoken of in hushed voices.
I was part of this community where life rested on the orders our small factories got. To get those sales orders we had to compete with firms in places like New Jersey, Canada, and even California firms that conducted their marketing in Nevada, or at sea. Some of those firms employed women hired by different agencies, and not all of them were free and safe and spoke English.
In this city the firms indirectly arrange for the girls through an agency that shares profits. The girls control their agency which vets and trains them, plus provides legal protection and security to all. In effect they provide a safe haven where a girl is free to make a living on her back. Also, she can enter and exit the business at her own prerogative, as we saw with Ms. Vee, who was married last weekend, and myself, who was a widow with needs and was now on her second informal assignment.
I explained that, for a new entrant who wants to try the business the deal is to get up to 5 ‘trial runs’ to get her toes wet before she has to join the union. I was registered as “Evie Jones” and Mr. G’s vendor was my sponsor for my ‘trial run.’
I saw how Ariel paid attention to this detail, maybe she was thinking of herself or her family firm - they had sales meetings for their product, but in their company town in Kansas they had no similar arrangements for escorts. For years that was not an issue, US customers had to come to their office in rural Kansas. But worldwide business was getting more competitive, more than half of their regular customers were exploring getting product from India and China. Mr. G’s economic moat was getting smaller and the whole family knew it.